Synthesis, spectroscopic studies of novel N-substituted phthalimides and evaluation of their antibacterial, antioxidant, DNA binding and molecular docking studies

Abstract

A new series of N-substituted phthalimide derivatives were prepared by condensation of appropriate amount of n-amino tetrachlorophthalimide with respective aldehyde in glacial acetic acid. The structural investigation of the synthesized compounds was done by spectroscopic methods (UV-Vis., IR, 1 H and 13 C NMR) and elemental analysis. The antibacterial screening of these compounds was performed against Escherichia coli and Staphylococcus mutans. The synthesized compounds were evaluated for their antioxidant potential using 2,2-diphenyl-1-picrylhydrazyl (DPPH) as a scavenging agent. The interaction ability of most promising compounds (3a and 3b) with native calf thymus DNA (Ct-DNA) was also studied by means of UV-Vis., circular dichroism (CD), viscosity measurements and thermal studies. The intrinsic binding constants (Kb) of 3a and 3b with Ct-DNA obtained from UV-Vis. absorption studies were 8 × 10 4 and 1 × 10 5 , respectively. Molecular docking of target compounds (3a and 3b) against DNA dodecamer d (CGCGAATTCGCG)2 has been carried out. The test compounds exhibited remarkable antibacterial, antioxidant and DNA binding activities. Article Info

Experimental and molecular docking investigation on DNA interaction of N‐substituted phthalimides: antibacterial, antioxidant and hemolytic activities

“…Phthalimide‐containing molecules can easily bind to various biopolymers such as DNA, RNA, proteins etc. This may be credited to their planar aromatic ring and hydrophobicity . As a consequence, extensive research has been devoted to the synthesis of novel phthalimide analogues in drug chemistry.…”

Crystal structure of 3-(benzo[d]thiazol-2-ylamino)isobenzofuran-1(3H)-one, C15H10N2O2S

“…Some enzymes play an important role in protecting human bodies from being injured by free radicals [5,6]. It is noteworthy that non-enzymes have been reported to possess antioxidant activities, including phenolic compounds [7], chalcone derivatives, phthalimide derivatives [8][9][10] and, coordination compounds [11][12][13].…”

Kinetic Studies, Antioxidant Activities, Enzyme Inhibition Properties and Molecular Docking of 1,3-Dihydro-1,3-Dioxoisoindole Derivatives

“…A plausible acid-catalysed hydrolysis mechanism of the synthesized compounds Scheme 4. The offer reactions of DPPH˙ and ABTS˙⁺ scavenging of the synthesized compounds taOves [52] studied that the DPPH˙ scavenging activity (IC 50 ) of the N-(4-methylphenyl)phthalimide, and N-(4-chlorophenyl)phthalimide as 1.30 ± 0.05, and 1.40 ± 0.06 mg/mL, respectively, and the ascorbic acid standard as 0.10 ± 0.03 mg/mL. In our study, this assay observed N- (4-methylphenyl)phthalimide, and N-(4-chlorophenyl) phthalimide had lower activity.…”